CN100567231C - 螺环戊菲芴基化合物及使用该化合物的有机电致发光装置 - Google Patents
螺环戊菲芴基化合物及使用该化合物的有机电致发光装置 Download PDFInfo
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- CN100567231C CN100567231C CNB2005100044369A CN200510004436A CN100567231C CN 100567231 C CN100567231 C CN 100567231C CN B2005100044369 A CNB2005100044369 A CN B2005100044369A CN 200510004436 A CN200510004436 A CN 200510004436A CN 100567231 C CN100567231 C CN 100567231C
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- fluorenes
- fragrance
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- 230000014509 gene expression Effects 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
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- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
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- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
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- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
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- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/115—Polyfluorene; Derivatives thereof
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Abstract
本发明涉及一种含有环戊菲和芴的螺基化合物以及一种有机电致发光装置。含有环戊菲和芴的螺基化合物能够容易地制备，以具有高的可溶性、高的色纯度和好的热稳定性。含有环戊菲和芴的螺基化合物适合作为有机膜的物质，特别是有机电致发光装置的发射层。此外，含有环戊菲和芴的螺基化合物可以被用作有机染料或者诸如非线性光学材料的电子材料。
Description
技术领域
本发明涉及一种基于螺环戊菲芴的化合物以及使用该化合物的有机电致发光装置，更特别地是，涉及一种具有蓝色发光特性的基于螺环戊菲芴的化合物，以及一种包括有机膜的有机电致发光装置，该有机膜含有该化合物以提高色纯度和发光效率。
背景技术
剑桥大学使用聚亚苯基亚乙烯基(PPV)膜已经开发出一种有机电致发光装置。PPV膜是一种共轭聚合物，通过湿涂布PPV而制得。PPV基的共轭聚合物被公开后，Covion公司开发了一种新的PPV类型的聚合物，其在有机溶剂中是可溶的。该聚合物的化学稳定性和发光效率都是优异的。Dow
Chemical公司开发了一种发射层形成材料基于聚芴的化合物，其优于PPV类型的聚合物。基于聚芴的化合物被认为是一种蓝色发光聚合物。然而，基于聚芴的化合物的色纯度没有达到希望的水平，这是由于聚芴结构的侧链上产生的激基缔合物(excimer)造成的(美国专利5,900,327)。因此，需要开发出一种具有高色纯度的基于聚芴的化合物。
为了提高聚芴的色纯度特性，美国专利5,621,131公开了一种含有聚螺芴的发光材料，美国专利5,763,636和5,859,211公开了具有螺二芴或含有杂原子的螺芴的发光材料。
然而，使用迄今所开发的发光材料的有机电致发光装置在效率、色纯度和寿命特性方面还没有达到希望的水平。
发明内容
本发明提供一种新的蓝色发光材料的螺环戊菲芴化合物，以及一种包括有机膜的有机电致发光装置，该有机膜含有该化合物以提高发光效率、热稳定性、色纯度和寿命特性。
根据本发明的一个方面，提供一种式1表示的基于螺环戊菲芴的化合物：
[式1]
其中X是C、N、O、S或Si；
每个R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12独立地选自H、羟基、取代或未取代的氨基、氰基、卤素原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C6-C30芳基(ayrl)、取代或未取代的C6-C30芳烷基和取代或未取代的C2-C30杂芳基，其中选自R1、R2、R3、R4、R5、R6、R7和R8的至少两个邻接的取代基与R9和R10，和R11和R12中至少之一彼此连接形成饱和或未饱和的环；m是2-5000的实数。
本发明还提供一种包括介于一对电极之间的有机层的有机电致发光装置，其中有机层含有基于螺环戊菲芴的化合物。
具体实施方式
本发明提供一种式1表示的基于螺环戊菲芴的化合物，更特别地是，提供一种式2表示的进一步包括亚芳基(Ar)重复单元的基于螺环戊菲芴的化合物。在式2中，n是基于螺环戊菲芴的化合物重复单元相对总聚合物的混合比，1-n是Ar重复单元相对总聚合物的混合比。
[式2]
其中，Ar是取代和未取代的C6-C30亚芳基、取代和未取代的C2-C30杂亚芳基或者取代和未取代的C2-C30杂环基；R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12如以上式1中的描述；m是2-5000的实数；n是0.01-1.0的实数。
在式2中，n是0.01-1.0的实数，并优选0.5-1.0。选自R1、R2、R3、R4、R5、R6、R7和R8的至少两个邻接的取代基与R9和R10，和R11和R12中至少之一彼此连接形成饱和和未饱和的C3-C50环。在这种情况下，该环可以含有诸如N、O、S等的杂原子。
在式1和2中，取代到每个烷基、环烷基、烷氧基、芳基、芳烷基、杂芳基、氨基和/或杂环基的取代基独立地为C1-C12烷基；C1-C12烷氧基；诸如F和C1的卤素原子；C1-C12烷基氨基；羟基；硝基；氰基；取代或未取代的氨基，如-NH2、-NH(R)或-N(R′)(R″)，其中每个R′和R″独立地为C1-C12烷基；羧基；磺酸；磷酸；C1-C12卤代烷基；C2-C12链烯基；C2-C12炔基；C2-C12杂烷基；C6-C30芳基；C6-C30芳烷基；C2-C30杂芳基；或者C2-C30杂芳烷基。
式2中的Ar单元具有式3表示的结构之一，并优选吩噁嗪结构。
[式3]
其中Y是O或S；每个R13、R14、R15和R16独立地选自H、羟基、取代或未取代的氨基、氰基、卤素原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C6-C30芳基和取代或未取代的C2-C30杂芳基。
式1表示的基于螺环戊菲芴的化合物例如可以是式4表示的化合物。
[式4]
其中m是2-5000的实数。
式2表示的化合物例如可以是式5表示的化合物。
[式5]
其中R18是C1-C12烷基；n是0.01-0.99的实数；m是2-5000的实数。
式5表示的化合物的一个示例性实施方案是式6表示的化合物。
[式6]
其中n是0.01-0.99的实数，m是2-5000的实数。
根据本发明的基于螺环戊菲芴的化合物可以通过聚合含有基于螺环戊菲芴的化合物的单体而得到。可选地，新的基于螺环戊菲芴的化合物与含有卤化物的Ar单体共聚，从而产生根据本发明的基于螺环戊菲芴的化合物。如上所述，该化合物易于制备。此外，该化合物具有高的可溶性、良好的色稳定性和强的热稳定性。因此该化合物可用于形成有机电致发光装置的有机膜。
含有式1重复单元的基于螺环戊菲芴的化合物的重复单元的聚合度可以为15或更大，优选为15-200。在此情况下，聚合物的数均分子量可以大于10000，优选为10000-200000，更优选为10000-100000。当聚合物的数均分子量保持在此范围内时，聚合物可以有例如优异的成膜特性。
使用有机膜，特别是含有式1表示的基于螺环戊菲芴的化合物的发射层来制备根据本发明的有机电致发光装置。在此情况下，式1表示的基于螺环戊菲芴的化合物可被用作发射层形成材料，特别是作为蓝色发光材料。此外，该化合物可被用于形成有机膜，例如空穴传输层和电子传输层。
式1表示的基于螺环戊菲芴的化合物可被单独用于形成发射层，还可以与普通掺杂剂一起用于形成发射层。如果该化合物与普通掺杂剂一起使用，式1表示的基于螺环戊菲芴的化合物的量可以为30-80重量份，基于100重量份的发射层形成材料的总重量。形成含有基于螺环戊菲芴的化合物的发射层可以使用例如真空沉积、溅射、印刷、涂层、喷墨印刷以及使用电子束的方法。
有机膜可以具有50-100nm的厚度。除了发射层，有机膜可以包括一种由有机化合物组成的膜，例如电子传输层和空穴传输层。
有机电致发光装置可以具有一种熟知的结构，包括阳极/发射层/阴极结构、阳极/缓冲层/发射层/阴极结构、阳极/空穴传输层/发射层/阴极结构、阳极/缓冲层/空穴传输层/发射层/阴极结构、阳极/缓冲层/空穴传输层/发射层/电子传输层/阴极结构以及阳极/缓冲层/空穴传输层/发射层/空穴阻挡层/阴极结构，但并不限于此。
本发明可以使用通常用于形成缓冲层的任何材料。优选地，形成缓冲层可以使用PEDOT/PSS、铜酞菁、聚噻吩、聚苯胺、聚乙炔、聚吡咯、聚亚苯基亚乙烯基或其衍生物，但并不限于此。
本发明可以使用通常用于形成空穴传输层的任何材料。空穴传输层可以是聚三苯基胺，但并不限于此。
本发明可以使用通常用于形成电子传输层的任何材料。电子传输层可以是聚噁二唑，但并不限于此。
本发明可以使用通常用于形成空穴阻挡层的任何材料。空穴阻挡层可以是LiF、BaF2或MgF2，但并不限于此。
有机电致发光装置能够以使用普通发光材料的方法制备，而不用特别的仪器和方法。
以下将参考下面的实施例进一步描述本发明。下面的实施例是为了说明的目的，而不是试图限制本发明的范围。
制备实施例1：2，7-二溴芴-4-酮的制备
将0.3g的CrO3加入溶于97mL的叔丁基氢过氧化物(butyhydroperoxide)(70wt％的水溶液)的18.9g(58.32mmol)的2，7-二溴芴中，并在室温下搅拌12小时。
反应完成后，用300mL的二氯甲烷萃取反应混合物。用水洗涤通过萃取得到的有机层，干燥，然后浓缩，得到黄色固体。向黄色固体添加乙酸乙酯进行重结晶，产生16.3g的目标物质(82.6％)。
1H-NMR(CDCl3)：ppm 7.35、7.38(2H，d)、7.60、7.606(2H，d，J＝1.8Hz)、7.62、7.63(2H，d，J＝1.83Hz)、7.744、7.749(2H，d，J＝1.65Hz)
制备实施例2：4-(4H-环戊[def]菲基)-2，7-二溴-4-螺芴的制备
将2-溴菲(参见：Synthetic communication，9(5)，377(1979)，20g，77.8mmol)溶解在300mL的无水THF中，然后冷却到-78℃。向其中加入62.4mL的2.5M的正丁基锂(156mmol)，然后在冷环境下搅拌30分钟。向所得混合物中缓慢加入溶于500mL的无水THF中的24.67g(73mmol)的2，7-二溴芴-4-酮，然后在冷却下搅拌30分钟。
用水终止反应后，所得混合物用乙酸乙酯萃取、干燥、过滤并浓缩。产物用柱色谱进行纯化，使用体积比为1∶8的乙酸乙酯和己烷的混合溶剂，得到4-(菲基)-2，7-二溴芴-4-醇。
将12.3g(22.86mmol)的4-(菲基)-2，7-二溴芴-4-醇溶解在120mL的乙酸中，加入5滴浓HCl，然后回流2小时。
反应完成后，用乙酸乙酯萃取所得混合物，洗涤，干燥，回流，然后浓缩。然后使用柱(溶剂∶己烷)分离浓缩的产物，得到5.7g的目标物质(产率：47.97％)。
1H-NMR(CDCl3)：ppm 6.47、6.85、6.90(4H，2m)、7.14、7.26(4H，2m)、7.51(4H，m)、7.69、7.78、7.98(2H，3m)
MASS(m/z)：500(M+2)、419、339、263、207、169
制备实施例3：聚(螺环戊菲芴)的制备
用具空和氮气置换完全除去Schlenk烧瓶内的水分。在手套箱(glove box)内，将0.444g(1.614mmol)的双(1，5-环辛二烯)镍(O)和0.252g(1.614mmol)的2，2′-二吡啶注入Schlenk烧瓶中，然后用真空和氮气置换Schlenk烧瓶内部。
然后在氮气气氛下，将8ml无水的二甲基甲酰胺(DMF)、0.2ml的1，5-环辛二烯(COD)(cyclooxtadiene)和8ml的无水甲苯加入其中，然后在70℃搅拌30分钟。然后，将制备实施例2制备的0.402g(0.807mmol)的4-(4H-环戊[def]菲基)-2，7-二溴-4-螺芴在8ml甲苯中的稀溶液加入混合物中。反应混合物在70℃回流24小时，然后冷却到室温。
使用含有HCl、丙酮和甲醇(体积比为1∶1∶2)的酸溶液处理反应混合物，产生沉淀。使用甲苯和甲醇纯化所得沉淀，然后用索氏提取器进行处理(产率：70％)。用凝胶渗透色谱法(GPC)测量所得聚合物的分子量。数均分子量(Mn)约为75000。
制备实施例4：螺环戊菲芴-吩噁嗪共聚物(摩尔比95∶5)的制备(参考反应
流程1)
[反应流程1]
用真空和氮气置换完全除去Schlenk烧瓶内的水分。在手套箱内，将0.465g(1.690mmol)的双(1，5-环辛二烯)镍(O)和0.264g(1.690mmol)的2，2′-二吡啶注入Schlenk烧瓶中，然后用真空和氮气置换Schlenk烧瓶内部。
然后在氮气气氛下，将4ml无水的二甲基甲酰胺(DMF)、0.2ml的1，5-环辛二烯(COD)和8ml的无水甲苯加入其中，然后在70℃搅拌30分钟。然后，将制备实施例2制备的0.400g(0.803mmol)的4-(4H-环戊[def]菲基)-2，7-二溴-4-螺芴和0.023g(0.042mmol)的3，7-二溴-10-[4-(2-乙基-己氧基)-苯基]-10，10a-二氢-4H-吩噁嗪在8ml甲苯中的稀溶液加入混合物中。反应混合物在70℃回流24小时，然后冷却到室温。
使用含有HCl、丙酮和甲醇(体积比为1∶1∶2)的酸溶液处理反应混合物，产生沉淀。使用甲苯和甲醇纯化所得沉淀，然后用索氏提取器进行处理(产率：65％)。用凝胶渗透色谱法(GPC)测量所得聚合物的分子量。数均分子量(Mn)约为78000。
实施例1：有机电致发光装置的制备
将氧化铟锡(ITO)涂覆到基底上，形成具有ITO层的透明电极基底。用光致抗蚀剂树脂和蚀刻剂以希望的形式使ITO层形成图案，并用UV进行清洗。然后，在形成图案的ITO层上涂覆约80nm厚的Batron P 4083(由拜尔公司得到)。形成导电的缓冲层，然后在180℃烘焙约1小时。然后，将根据制备实施例4制得的聚合物溶于甲苯，制得聚合物溶液。使用聚合物溶液旋涂缓冲层，然后在真空烘箱中烘焙，完全除去溶剂，形成发射层。在此情况下，旋涂前用0.2mm过滤器过滤聚合物溶液。此外，控制聚合物溶液的浓度和旋转速度，使得聚合物膜的厚度约为80nm。然后，在保持4x10-6乇(torr)或更小的真空度下，使用真空沉积设备在发射层上依次沉积Ca和Al。沉积过程中，用晶体探测器(crystal sensor)控制膜的厚度和生长速率。以上述方式制备的电致发光(EL)装置具有ITO/PEDOT/发光聚合物/Ca/Al的结构，发光面积为4mm2。
可以容易地制备根据本发明的基于螺环戊菲芴的化合物，以具有高的可溶性、高的色纯度、好的色稳定性和好的热稳定性。因此，基于螺环戊菲芴的化合物适合作为有机膜的基底，特别是有机电致发光装置的发射层。此外，该化合物可以被用作有机染料或者诸如非线性光学材料的电子材料。
尽管参考示例性的实施方案已经对本发明进行了具体说明和描述，但本领域普通技术人员应当理解，可以在形式和细节上对本发明进行各种变化，而该变化并不会偏离如权利要求所定义的本发明的精神和范围。
Claims (9)
1.一种式2表示的的基于螺环戊菲芴的化合物：
[式2]
其中，Ar具有式3表示的结构：
[式3]
其中每个R13、R14和R15独立地选自H、羟基、取代或未取代的氨基、氰基、卤素原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C6-C30芳基和取代或未取代的C2-C30杂芳基；
X是C；
每个R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12独立地选自H、卤素原子、羟基、取代或未取代的氨基、氰基、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基和取代或未取代的C2-C30杂芳基，其中选自R1、R2、R3、R4、R5、R6、R7和R8的至少两个邻接的取代基与R9和R10、以及R11和R12中至少之一彼此连接形成饱和或未饱和的环；和
其中取代基独立地为C1-C12烷基；C1-C12烷氧基；卤素原子；C1-C12烷基氨基；羟基；硝基；氰基；-NH2或-N(R′)(R″)，其中每个R′和R″独立地为C1-C12烷基；羧基；磺酸；磷酸；C1-C12卤代烷基；C2-C12链烯基；C2-C12炔基；C2-C12杂烷基；C6-C30芳基；C6-C30芳烷基；C2-C30杂芳基；或者C2-C30杂芳烷基；
m是2-5000的实数；和
n是0.01-1.0的实数。
2.权利要求1的基于螺环戊菲芴的化合物，其中在取代基中，卤素为F或Cl。
3.权利要求1的基于螺环戊菲芴的化合物，以式5表示：
[式5]
其中R18是C1-C12烷基；n是0.01-0.99的实数；m是2-5000的实数。
4.权利要求3的基于螺环戊菲芴的化合物，以式6表示：
[式6]
其中n是0.01-0.99的实数，m是2-5000的实数。
5.一种包括介于一对电极之间的有机膜的有机电致发光装置，其中所述有机膜含有式2表示的基于螺环戊菲芴的化合物：
[式2]
其中，Ar具有式3表示的结构：
[式3]
每个R13、R14和R15独立地选自H、羟基、取代或未取代的氨基、氰基、卤素原子、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C6-C30芳基和取代或未取代的C2-C30杂芳基；
X是C；
每个R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12独立地选自H、卤素原子、羟基、取代或未取代的氨基、氰基、取代或未取代的C1-C20烷基、取代或未取代的C3-C20环烷基、取代或未取代的C1-C20烷氧基、取代或未取代的C6-C30芳基、取代或未取代的C6-C30芳烷基和取代或未取代的C2-C30杂芳基，其中选自R1、R2、R3、R4、R5、R6、R7和R8的至少两个邻接的取代基与R9和R10、以及R11和R12中至少之一彼此连接形成饱和或未饱和的环；和
其中取代基独立地为C1-C12烷基；C1-C12烷氧基；卤素原子；C1-C12烷基氨基；羟基；硝基；氰基；-NH2或-N(R′)(R″)，其中每个R′和R″独立地为C1-C12烷基；羧基；磺酸；磷酸；C1-C12卤代烷基；C2-C12链烯基；C2-C12炔基；C2-C12杂烷基；C6-C30芳基；C6-C30芳烷基；C2-C30杂芳基；或者C2-C30杂芳烷基；
m是2-5000的实数；和
n是0.01-1.0的实数。
6.权利要求5的有机电致发光装置，其中在取代基中，卤素为F或Cl。
7.权利要求5的有机电致发光装置，其中有机膜是发射层、空穴传输层或者电子传输层。
8.权利要求5的有机电致发光装置，其中化合物以式5表示：
[式5]
其中R18是C1-C12烷基；n是0.01-0.99的实数；m是2-5000的实数。
9.权利要求8的有机电致发光装置，其中化合物以式6表示：
[式6]
其中n是0.01-0.99的实数，m是2-5000的实数。
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| KR101202340B1 (ko) * | 2005-01-21 | 2012-11-16 | 삼성디스플레이 주식회사 | 청색 발광 화합물 및 이를 채용한 유기 전계 발광 소자 |
| JP5407122B2 (ja) * | 2006-08-01 | 2014-02-05 | 住友化学株式会社 | 高分子化合物および高分子発光素子 |
| JP5680301B2 (ja) * | 2006-10-11 | 2015-03-04 | ユニバーシティ オブ フロリダ リサーチ ファンデーション インコーポレーティッド | ペンダントパイ相互作用性／結合性置換基を含有する電気活性ポリマー、そのカーボンナノチューブ複合体、およびその形成方法 |
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| KR101453873B1 (ko) * | 2007-10-08 | 2014-10-24 | 삼성디스플레이 주식회사 | 사이클로펜타페난트렌계 화합물 및 이를 이용한 유기 발광소자 |
| KR101473306B1 (ko) | 2007-11-05 | 2014-12-16 | 삼성디스플레이 주식회사 | 사이클로펜타페난트렌계 화합물 및 이를 이용한 유기 전계발광 소자 |
| US9153790B2 (en) * | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| DE102010033080A1 (de) * | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
| JP5901167B2 (ja) * | 2010-10-27 | 2016-04-06 | キヤノン株式会社 | スピロ［シクロペンタ［ｄｅｆ］トリフェニレン−４，９’−フルオレン］化合物及びそれを有する有機発光素子 |
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